16669-99-1

Basic information

• Product Name: 2'-HYDROXY-3,4-METHYLENEDIOXYCHALCONE
• Synonyms: 2'-HYDROXY-3,4-METHYLENEDIOXYCHALCONE;3-(1,3-BENZODIOXOL-5-YL)-1-(2-HYDROXYPHENYL)PROP-2-EN-1-ONE;2'-HYDROXY-2-PIPERONYLIDENEACETOPHENONE;3-Benzo[1,3]dioxol-5-yl-1-(2-hydroxy-phenyl)-propenone
• CAS NO: 16669-99-1
• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.26
• Mol File: 16669-99-1.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 459.1°Cat760mmHg
• Flash Point: 174.8°C
• Appearance: /
• Density: 1.345g/cm³
• Vapor Pressure: 4.75E-09mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: 2'-HYDROXY-3,4-METHYLENEDIOXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-HYDROXY-3,4-METHYLENEDIOXYCHALCONE(16669-99-1)
• EPA Substance Registry System: 2'-HYDROXY-3,4-METHYLENEDIOXYCHALCONE(16669-99-1)

Safety Data

• Hazardous Substances Data: 16669-99-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H12O4/c17-13-4-2-1-3-12(13)14(18)7-5-11-6-8-15-16(9-11)20-10-19-15/h1-9,17H,10H2

Upstream product

• 120-57-0 piperonal 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 2620-47-5 1-(benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol 
• 118-93-4 o-hydroxyacetophenone 
• 32865-61-5 2-iodophenyl acetate 
• 261785-32-4 3-(o-acetoxyphenyl)-1-(3',4'-methylenedioxyphenyl)prop-2-yn-ol 

Downstream Products

• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 
• 54401-45-5 2-(benzo[d][1,3]dioxol-5-yl)-4H-chromen-4-one 
• 873934-69-1 2-[2-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydrobenzo-[b][1,4]thiazepin-4-yl]phenol 
• 36136-89-7 3-(3,4-methylenedioxy-phenyl)-4-chromone 
• 36685-58-2 3',4'-methylenedioxyaurone 
• 54401-46-6 2-(benzo[d][1,3]dioxol-5-yl)chroman-4-one 
• 56202-04-1 1-(2-hydroxyphenyl)-3-(3,4-methylenedioxyphenyl)propanone 
• 109255-62-1 (4-benzo[1,3]dioxol-5-yl-3,4-dihydro-2H-pyrazol-3-yl)-(2-hydroxy-phenyl)-ketone 

Relevant articles and documents

SAR Studies and Biological Characterization of a Chromen-4-one Derivative as an Anti- Trypanosoma brucei Agent

Chemical modulation of the flavonol 2-(benzo[d][1,3]dioxol-5-yl)-chromen-4-one (1), a promising anti-Trypanosomatid agent previously identified, was evaluated through a phenotypic screening approach. Herein, we have performed structure-activity relationsh

The synthesis and synergistic antifungal effects of chalcones against drug resistant Candida albicans

To identify effective and low toxicity synergistic antifungal compounds, 24 derivatives of chalcone were synthesized to restore the effectiveness of fluconazole against fluconazole-resistant Candida albicans. The minimal inhibitory concentration (MIC80) and the fractional inhibitory concentration index (FICI) of the antifungal synergist fluconazole were measured against fluconazole-resistant Candida albicans. This was done via methods established by the clinical and laboratory standards institute (CLSI). Of the synthesized compounds, 2′-hydroxy-4′-methoxychalcone (8) exhibited the most potent in vitro (FICI = 0.007) effects. The structure activity relationship of the compounds are then discussed.

QSAR, in silico docking and in vitro evaluation of chalcone derivatives as potential inhibitors for H1N1 virus neuraminidase

Thirty three chalcones were synthesized and tested on viral H1N1 neuraminidase activity by using MUNANA assay [2′-(4-methylumbelliferyl)-α-d-N-acetylneuraminic acid] assay with DANA (2,3-didehydro-2-deoxy-N-acetylneuraminic acid) was used as standard. 2D and 3D-quantitative structure?activity relationship models have been successfully developed with a good correlative and predictive ability for quantitative structure?activity relationships of these chalcone derivatives. Result from the 2D-quantitative structure?activity relationship model indicates that electrostatic parameter enhanced bioactivity of the chalcones while steric substituents diminished their potency as H1N1 neuraminidase inhibitors. 3D-quantitative structure?activity relationship model showed the importance of the position of the hydroxyl group in chalcone derivatives which can influence on hydrophobicity, hydrogen bond donor and aromatic ring features that enhance the biological activity. Finally, docking studies showed that chalcones MC8 and MC16 with low C docker interaction energies and higher numbers of hydrogen bonding have better inhibitory activity against viral H1N1 neuraminidase.